Attempt 2 - Plex Media Server on Pi | VPN?

FIRST, I APOLOGIZE FOR THE LENGTH OF THIS POST; I NEED TO BE AS DETAILED AS POSSIBLE DUE TO MY NEWNESS/"GREENNESS" AS A RELATIVE NEWCOMER TO THE WORLD OF PI/NETWORKING/VPN/IP/ETC.

BACKGROUNDI am a Cox Communications Panoramic Wi-Fi customer with high-speed Internet as part of the package. I have the following computers in our family: (1) a Raspberry Pi 3 B+ running Raspbian with the MATE DE added thereto (connected via Ethernet to the Cox router); (2) a Dell Dimension E521 (AMD Sempron processor running @ 1.8GHz) with 4GB RAM running Linux Mint 18.3 with the MATE DE added thereto (connected to Wi-Fi via a USB adapter); and (3) an RCA Cambio (10.1" laptop/tablet hybrid) running on an Intel Atom processor @ 1.4GHz with 2 GB RAM running Windows 10 Home (connected to Wi-Fi using the Cambio's built-in Wi-Fi capability). I have the following iPhone models in our family: the 6s (2), the 8, & the 8 Plus, all of which have unlimited data through our carrier (T-Mobile). I also have 3 tablets in our family: 1 Kindle Fire 7HD and 2 ASUS Android 4.somethings. Finally, I have 3 Smart TVs in our family, all of which are connected via Wi-Fi and that have the Plex app.

GOALI want to be able to run Plex Media Server on the Pi AND to be able to connect to Plex Media Server from any device listed above (or from any other Internet-connected device) to display photos, stream music, & stream videos. I have an NTFS-formatted Toshiba 1TB USB hard drive that I will connect to a USB hub (and the hub into the Pi); I'm told I'll need to install ntfs-3g on the Pi to allow the Pi to read the media file types contained thereon (& I know that ntfs-3g will have to be installed on the Dell, as well, to allow me to be able to add files from the Dell and to be able to allow the Dell to view/play said media files, if desired).

Realizing the importance of a secure connection to the Plex Media Server, I was strongly advised to have a VPN service in-place before setting up the Plex Media Server on the Pi; such advice is excellent and that I fully intend to heed. At the same time, however, I do want to achieve the best-possible balance between the cost and the security of any connection to the Plex Media Server.

I also know that, although I've reserved IP addresses within my Cox router for the Pi, the Dell,& the Cambio, as well as 2 HP wireless-capable printers, I'll need to signup with a Dynamic DNS (DDNS) service to connect where the connection should be made since Cox assigns a dynamic, rather than a static, IP address for residential customers. The Cox router lists 6 DDNS providers that are supported; I'm leaning toward NoIP, currently.

SIDE THOUGHTSome might suggest running Plex Media Server on the 4GB Dell PC, but I don't think that'd be best for 2 reasons: (1) it's only got a Wi-Fi connection (my house is not wired for Ethernet; the Dell is located in my office - as such, I use it for "PC-type duties" (e-mail/web-browsing/tracking finances/creating and analyzing budgets/Word document creation, editing, & printing/Excel spreadsheet creation, editing, & printing/PDF viewing & printing - you get the idea (and I don't want to have an Ethernet cable snaking along the baseboards between the 2 rooms involved (the Cox router & the Raspberry Pi 3 B+ are in the bonus room, which also serves as an unofficial "media room") & (2) its only video output option is VGA, so it doesn't have the graphics processing power to decode HD video streams "on the fly", like the Pi 3 B+ has. Trust me when I say that I've tried to play HD video on it via Netflix and YouTube; within seconds, the web browser was closed and another option was immediately chosen!

QUESTIONShould I proceed with configuring a VPN server on the Pi (i.e., PiVPN) OR should I signup for a VPN service?

FOLLOW-UP QUESTIONIf I signup for a service, how will I know how many simultaneous connections I'll need? Since there are only 4 people in my family (counting myself), I don't foresee a scenario in which more than 4 connections to the Plex Media Server would be necessary. That leads me to believe I would need to allow for up to 4 simultaneous connections. But, any device would connect to the Cox router via a VPN, so maybe only 1 connection is needed? I have no idea at this point - thus the reason for this post.

Please pardon my newness/"greenness" to this area; I've used Windows OSes since 3.0, Mac OS X Yosemite & Mac OS X El Capitan, & just started using Linux - not very long ago at all - maybe within the past month, but with much higher usage in the past week.

I'm also working on setting up RealVNC to connect from any computer to either of the other computers (with all possibilities & in all directions). Each computer has VNC Viewer, as well as VNC Connect/VNC Server (whatever the server product of RealVNC is being called, currently). The final thing I'll say is this: on the Cambio (running Windows 10 Home), I'd like to be able to see the Pi & the Dell under "Network" in Windows Explorer. Similarly, on the Pi & the Dell, I'd like to be able to see the other 2 computers in the Files app's Network section.

I sincerely hope I'm not overwhelming anybody, but this is far more involved than I had originally imagined. I'm up to the challenge, but I just need a little (OK - A LOT OF!) help from anyone who's been "around the block".

(06-22-2018, 12:04 PM)I REALLY NEED SOME DETAILED AND STEP-BY-STEP HELP. I AM NEW TO ALL OF THIS. PLEASE, SOMEONE HELP. I AM GETTING DIFFERENT ANSWERS FROM DIFFERENT PEOPLE IN OTHER PLACES ONLINE. I KNOW THIS CAN BE ACHIEVED; I JUST NEED HELP FROM SOMEONE WHO HAS ACHIEVED IT THEMSELF.Mark the Auditor Wrote: FIRST, I APOLOGIZE FOR THE LENGTH OF THIS POST; I NEED TO BE AS DETAILED AS POSSIBLE DUE TO MY NEWNESS/"GREENNESS" AS A RELATIVE NEWCOMER TO THE WORLD OF PI/NETWORKING/VPN/IP/ETC.

BACKGROUNDI am a Cox Communications Panoramic Wi-Fi customer with high-speed Internet as part of the package. I have the following computers in our family: (1) a Raspberry Pi 3 B+ running Raspbian with the MATE DE added thereto (connected via Ethernet to the Cox router); (2) a Dell Dimension E521 (AMD Sempron processor running @ 1.8GHz) with 4GB RAM running Linux Mint 18.3 with the MATE DE added thereto (connected to Wi-Fi via a USB adapter); and (3) an RCA Cambio (10.1" laptop/tablet hybrid) running on an Intel Atom processor @ 1.4GHz with 2 GB RAM running Windows 10 Home (connected to Wi-Fi using the Cambio's built-in Wi-Fi capability). I have the following iPhone models in our family: the 6s (2), the 8, & the 8 Plus, all of which have unlimited data through our carrier (T-Mobile). I also have 3 tablets in our family: 1 Kindle Fire 7HD and 2 ASUS Android 4.somethings. Finally, I have 3 Smart TVs in our family, all of which are connected via Wi-Fi and that have the Plex app.

GOALI want to be able to run Plex Media Server on the Pi AND to be able to connect to Plex Media Server from any device listed above (or from any other Internet-connected device) to display photos, stream music, & stream videos. I have an NTFS-formatted Toshiba 1TB USB hard drive that I will connect to a USB hub (and the hub into the Pi); I'm told I'll need to install ntfs-3g on the Pi to allow the Pi to read the media file types contained thereon (& I know that ntfs-3g will have to be installed on the Dell, as well, to allow me to be able to add files from the Dell and to be able to allow the Dell to view/play said media files, if desired).

Realizing the importance of a secure connection to the Plex Media Server, I was strongly advised to have a VPN service in-place before setting up the Plex Media Server on the Pi; such advice is excellent and that I fully intend to heed. At the same time, however, I do want to achieve the best-possible balance between the cost and the security of any connection to the Plex Media Server.

I also know that, although I've reserved IP addresses within my Cox router for the Pi, the Dell,& the Cambio, as well as 2 HP wireless-capable printers, I'll need to signup with a Dynamic DNS (DDNS) service to connect where the connection should be made since Cox assigns a dynamic, rather than a static, IP address for residential customers. The Cox router lists 6 DDNS providers that are supported; I'm leaning toward NoIP, currently.

SIDE THOUGHTSome might suggest running Plex Media Server on the 4GB Dell PC, but I don't think that'd be best for 2 reasons: (1) it's only got a Wi-Fi connection (my house is not wired for Ethernet; the Dell is located in my office - as such, I use it for "PC-type duties" (e-mail/web-browsing/tracking finances/creating and analyzing budgets/Word document creation, editing, & printing/Excel spreadsheet creation, editing, & printing/PDF viewing & printing - you get the idea (and I don't want to have an Ethernet cable snaking along the baseboards between the 2 rooms involved (the Cox router & the Raspberry Pi 3 B+ are in the bonus room, which also serves as an unofficial "media room") & (2) its only video output option is VGA, so it doesn't have the graphics processing power to decode HD video streams "on the fly", like the Pi 3 B+ has. Trust me when I say that I've tried to play HD video on it via Netflix and YouTube; within seconds, the web browser was closed and another option was immediately chosen!

QUESTIONShould I proceed with configuring a VPN server on the Pi (i.e., PiVPN) OR should I signup for a VPN service?

FOLLOW-UP QUESTIONIf I signup for a service, how will I know how many simultaneous connections I'll need? Since there are only 4 people in my family (counting myself), I don't foresee a scenario in which more than 4 connections to the Plex Media Server would be necessary. That leads me to believe I would need to allow for up to 4 simultaneous connections. But, any device would connect to the Cox router via a VPN, so maybe only 1 connection is needed? I have no idea at this point - thus the reason for this post.

Please pardon my newness/"greenness" to this area; I've used Windows OSes since 3.0, Mac OS X Yosemite & Mac OS X El Capitan, & just started using Linux - not very long ago at all - maybe within the past month, but with much higher usage in the past week.

I'm also working on setting up RealVNC to connect from any computer to either of the other computers (with all possibilities & in all directions). Each computer has VNC Viewer, as well as VNC Connect/VNC Server (whatever the server product of RealVNC is being called, currently). The final thing I'll say is this: on the Cambio (running Windows 10 Home), I'd like to be able to see the Pi & the Dell under "Network" in Windows Explorer. Similarly, on the Pi & the Dell, I'd like to be able to see the other 2 computers in the Files app's Network section.

I sincerely hope I'm not overwhelming anybody, but this is far more involved than I had originally imagined. I'm up to the challenge, but I just need a little (OK - A LOT OF!) help from anyone who's been "around the block".